Issa Rae Heads Back to HBO With Vegas Boxing Comedy

HBO’s new pilot follows a barber and rising boxer whose friendship buckles under the weight of ambition, money, insecurity, and success.

ByBernadette Giacomazzo
August 25, 2026

Key Takeaways

• HBO ordered a pilot for Issa Rae’s Untitled Male Friendship Show, a half-hour comedy set in Las Vegas’ professional boxing scene.
• The series follows aspiring sports manager Menzel and rising boxer JB as ambition, money, insecurity, and success strain their friendship.
• Rae will write and executive produce, while Insecure collaborator Prentice Penny will serve as showrunner, executive producer, and pilot director.

Issa Rae is getting another shot at HBO — and this time, she’s stepping into the Las Vegas boxing scene.

According to Deadline, HBO has ordered a pilot for Rae’s Untitled Male Friendship Show, a half-hour comedy she wrote and will executive produce. The project centers on Menzel, a 30-year-old barber trying to break into sports management while serving as JB’s closest friend, a boxer whose career is taking off. Against the backdrop of professional boxing in Las Vegas, the series will explore how their friendship unravels as ambition, money, insecurity, and success put pressure on both men.

The project also reunites Rae with Prentice Penny, one of her key collaborators on Insecure. Penny will serve as showrunner, executive producer and director of the pilot. He previously earned an Emmy nomination for his work on Insecure and has credits including Brooklyn Nine-Nine, Happy Endings, Scrubs and Pause with Sam Jay.

Jax Clark will executive produce for Rae’s Hoorae, while Jonathan Berry and Dave Becky will executive produce through 3 Arts Entertainment.

The HBO order comes not long after Rae acknowledged that her current career moment had left her feeling restless. During an appearance on Kevin Fredericks’ Not My Best Moment podcast, she said her definition of success is closely tied to having a television project actively in production.

“I know that I appear successful to other people, but right now, no, I feel really stagnant,” Rae said. “Because I only feel successful when my sh*t is on the air. I don’t have sh*t on the air right now.”

That makes the new pilot a notable return to the network where Rae built much of her television career. Insecure, which Rae co-created with Larry Wilmore, ran for five seasons on HBO and earned 14 Emmy nominations, a Peabody Award and three Golden Globe nominations.

Rae later executive produced A Black Lady Sketch Show and created Rap Sh!t, which followed two friends trying to break into Miami’s rap industry and ran for two seasons.

Rae has also spoken about how earlier setbacks changed the way she approaches television. Looking back on the failed development of I Hate L.A. Dudes, she told Fredericks that she had become too willing to defer to people with more traditional industry experience.

“I forgot that they wanted to work with me because I’m me,” Rae said.

She eventually came away with a different understanding of what collaborators expected from her: “They want me to be as loud as possible with what I want to say.”

The new HBO pilot arrives during another transition in Rae’s business career. She signed a three-year first-look film and television deal with Paramount in January after previously holding an overall deal with HBO beginning in 2021. Deadline reported that the Vegas boxing project is believed to have been developed before the Paramount agreement.